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A kind of preparation method of cefazedone sodium compound

A technology of cefazedone sodium and its compound, which is applied in the field of preparation of anti-infective drug cefazedone sodium compound, can solve the problems of many side reactions, reduced total product yield, low yield of final product, etc., and achieves simple process route, The effect of high total yield and purity

Active Publication Date: 2020-05-19
SHANDONG YUXIN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Although the synthetic route is simplified, when intermediate d reacts with compound e for amidation reaction, the carboxyl group in intermediate d will participate in competing reactions, resulting in low yield of final product
[0014] There are many side reactions in the synthesis process in the above-mentioned route, so that the defect that the total yield of the product is reduced

Method used

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  • A kind of preparation method of cefazedone sodium compound
  • A kind of preparation method of cefazedone sodium compound
  • A kind of preparation method of cefazedone sodium compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of compound IV

[0032] Add 27.23g of 7-ACA(Ⅱ), 13.22g of compound III and 600ml of N,N-dimethylformamide to the reaction flask, control the temperature at 40-50℃ and stir the reaction for 3h. TLC monitors the completion of the reaction, and then removes it by evaporation Solvent, add 800ml ethyl acetate and 800ml saturated sodium bicarbonate to the obtained oil, separate the layers, dry the organic layer over anhydrous sodium sulfate, filter, concentrate the filtrate, and recrystallize with ether to obtain a solid 31.87g with a molar yield of 92.4% , HPLC purity is 99.86%.

Embodiment 2

[0034] Preparation of compound IV

[0035] Add 27.23g of 7-ACA(Ⅱ), 13.22g of compound III, and 600ml of dichloromethane to the reaction flask, control the temperature at 40-50℃ and stir for 3h. TLC monitors the completion of the reaction, then evaporates and removes the solvent to obtain an oily substance Add 800ml ethyl acetate and 800ml saturated sodium bicarbonate, separate the layers, the organic layer is dried over anhydrous sodium sulfate, filtered, the filtrate is concentrated and recrystallized with ether to obtain a solid 31.34g, molar yield 90.8%, HPLC purity 99.78% .

Embodiment 3

[0037] Preparation of compound IV

[0038] Add 27.23g of 7-ACA(Ⅱ), 14.54g of compound III and 600ml of N,N-dimethylformamide to the reaction flask, control the temperature at 40-50℃ and stir the reaction for 3h. TLC monitors that the reaction is complete, and then it is removed by evaporation. Solvent, add 800ml ethyl acetate and 800ml saturated sodium bicarbonate to the obtained oily substance, separate the layers, dry the organic layer over anhydrous sodium sulfate, filter, concentrate the filtrate, and recrystallize it with ether to obtain 32.29g solid with a molar yield of 93.6% , HPLC purity is 99.85%.

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Abstract

The invention discloses a preparation method of a cefazedone sodium compound. 7-ACA and a compound III react to prepare a compound IV, and the compound IV and a compound V have an amidation reaction,and are salified and refined to obtain a competitive product of cefazedone sodium (I). The process route of the reaction is simple, the total yield and the purity are high, and the method is suitablefor industrial production.

Description

Technical field [0001] The present invention belongs to the technical field of medicine, and specifically relates to a method for preparing an anti-infective drug cefazerone sodium compound. Background technique [0002] Cefazedone was developed by E Merck, Darmstadt laboratory in the late 1970s. It is the first-generation cephalosporin antibiotic. Cephalosporin is a semi-synthetic cephalosporin antibiotic, which achieves the purpose of inhibition and sterilization by interfering with and preventing the synthesis of bacterial cell walls. It has good antibacterial activity against common gram-positive and some gram-negative bacteria and some anaerobic bacteria. It can be used for respiratory system, urinary system, gastrointestinal infection, gynecology, peritoneum, skin, soft tissue and plastic surgery, etc. Sensitivity causes infection treatment. [0003] The chemical name of cefazidone sodium is: (6R, 7R)-3-(5-methyl-1,3,4-thiadiazolyl-2-mercaptomethyl)-7-(3,5-dichloro) -4-pyr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/36C07D501/06
CPCC07D501/06C07D501/36
Inventor 刘振腾董雪菊张园叶淼
Owner SHANDONG YUXIN PHARMA CO LTD
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